Synthesis and Molecular Recognition of Water‐Soluble S₆‐Corona[3]arene[3]pyridazines

Abstract

We report the efficient and scalable synthesis and molecular-recognition properties of novel and water-soluble S6-corona[3]arene[3]pyridazines. The synthesis comprises a one-pot nucleophilic aromatic substitution reaction between diesters of 2,5-dimercaptoterephthalate and 3,6-dichlorotetrazine followed by the inverse electron-demand Diels-Alder reaction of the tetrazine moieties with an enamine and exhaustive saponification of esters. The resulting S6-corona[3]arene[3]pyridazines, which adopt a 1,3,5-alternate conformation in the crystalline state, are able to selectively form stable 1:1 complexes with dicationic guest species in water with association constants ranging from (1.10±0.06)×10(3) M(-1) to (1.18±0.06)×10(5) M(-1). The easy availability, large cavity size, strong and selective binding power render the water-soluble S6-corona[3]arene[3]pyridazines useful macrocyclic hosts in various disciplines of supramolecular chemistry.

Molecular recognition and activation by polyaza macrocyclic compounds based on host–guest interactions

“…L 6 could be used as a fluorescence detector for sulfate anion in aqueous environment. 21 The synthesis comprises a one-pot nucleophilic aromatic substitution reaction between diesters of 2,5-dimercaptoterephthalate and 3,6-dichlorotetrazine, followed by the inverse electron-demand Diels-Alder reaction of the tetrazine moieties with an enamine and exhaustive saponification of esters. Wang group have synthesized a water-soluble S6-corona [3]arene [3]pyridazines (L 7 , Fig.…”

Synthesis and post-functionalization of alternate-linked-meta-para-[2n.1n]thiacyclophanes

“…Wang et al were the first to report a one-pot procedure towards the synthesis of various thiapillararenes [18–20]. Our group reported a disulfide-bridged [2 n ] pillararene-like molecule in a two-step procedure [21].…”

Synthesis, Structure, and Anion Binding Properties of Electron‐Deficient Tetrahomocorona[4]arenes: Shape Selectivity in Anion–π Interactions

“…On the basis of nucleophilic aromatic substitution reaction, we have established highly efficient one-pot reaction strategy [8][9][10][11][12][13] and stepwise fragment coupling approach [14,15] to construct corona[n]arenes (n = 5, 6, 8). Post-macrocyclization chemical manipulation methods [9-10, 13, 14] have also been developed to synthesize functional corona[n]arenes.Corona- [n]arenes have been demonstrated to be versatile and fascinating host molecules to complex anions,c ations,a nd neutral guest species.…”